Fair Use and Advocacy Strategies

The story in a nutshell: a professor at a Northeastern college asked
Siva for permission to distribute a copy of a chapter of
"Anarchist in the Library". [SF - elided, but perhaps critical,
is an aspect of "to the entire incoming class"]
"Of course," Siva replied, adding that [the professor] really ought
not to have asked. The professor responded by forwarding to Siva a
note from the college librarian, which warns firmly that "educational
purpose is only one of the four determining factors, and that the
courts have weighted one of them, the impact on the potential market,
heavily in recent cases." Siva, horrified, runs the use of the book
chapter through the four-factor test to show that the professor has a
slam-dunk "case."

After thinking about it for a while, and checking a few
fair use references,
(particularly the book interviews case cited there), I decided
Siva's analysis was probably right. But ... not so right that it
couldn't reasonably be contested by an "aggressive" plaintiff.
That is, I could see a publisher arguing that copying a whole chapter
was too much, it'd be distributed to too many people, the book itself
is quite new, digital copies even of a chapter could be hurtful to the
book's market, and so on. I don't think it would be a "silly" lawsuit.
A risk-averse person, or institution, would not be ridiculous to be
feel they had a non-negligible chance of losing. The professor definitely
wasn't wrong to ask. In fact that was the objectively right thing to do
(i.e., I don't mean that in terms of morality, I mean there is enough
doubt so they should indeed check about usage permission).

Note, regarding any irony of asking copyright reformers about using material,
I strongly dissent from the concept that anyone should
put too much stock in an author's good will or general policy advocacy. In the
face of a prospective lawsuit, there is very little consolation in being able
to say to a few friends, but-he's-a-hypocrite! (heck, some years ago,
Mike Godwin had a habit of both arguing prominently that
"Maybe libel law is obsolete", and at the exact same time,
saber-rattling libel lawsuit
at items which particularly offended him - and he'd happily explain why
it wasn't a contradiction, why this time was different - every time!).

As to how to attack the problem, education, advocacy, assistance, reform,
all are good ideas in themselves. But I'm afraid that my own
experiences
fighting for fair use make me even more pessimistic than Lessig.